MSP Chat

Coming to you live from Nerdio’s NerdioCon event in sunny Palm Springs, CA, Erick and Rich discuss why Anthropic’s new AI services venture for midsize businesses is the latest reason MSPs need to get moving on an AI strategy, as well as techniques for building a strategic, sticky AI roadmap for your customers. Then they’re joined by Nerdio President Joseph Landes for his take on underappreciated MSP opportunities in Microsoft 365, Azure Virtual Desktop, Windows 365, and Microsoft Copilot. And finally, one last thing: How Bebop the robot inadvertently delayed a flight to San Diego. Discussed in this episode:From Anthropic: Building a new enterprise AI services company with Blackstone, Hellman & Friedman, and Goldman SachsRobot passenger causes flight delay in California Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

In this special bonus episode of MSP Chat, sponsored by Datto, Erick and Rich discuss why cyber resilience services continue to be a source of revenue and growth for MSPs and what that says about how they should construct their service portfolio and refine their tool stack, as well as why client proposals are sales tools, not technical documents. Then they’re joined by Dan Tomaszewski, Kaseya’s EVP of channel, for a deep dive into some especially interesting findings in the 2026 Kaseya State of the MSP Report, and what MSPs should do in response. And finally, one last thing: An April Fool’s Day gag that turned into a hit product for chronic doom scrollers. Discussed in this episode:2026 Kaseya State of the MSP ReportOn-demand webinar: The MSP playbook: Insights from the 2026 State of MSP ReportWhich brand won April Fools in 2026? Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Live from the Kaseya Connect 2026 conference in Las Vegas, Erick and Rich discuss Kaseya’s giant AI platform rollout and strategies for turning your renewal process into a retention machine. Then they’re joined by Cynomi CEO David Primor for an insider’s take on the future of CISO services in the agentic AI era. And finally, one last thing: Who comes out ahead when a thief exchanges pasta for Legos? Discussed in this episode:MSP Chat Episode 88: From the Server Room to the BoardroomCynomi Redefines How MSPs Scale Cybersecurity Services and Growth with the Launch of New CISO Intelligence AI AgentsPolice arrest man who replaced US$34,000 worth of Lego pieces with pasta Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss why agentic AI makes business resilience versus just cyber resilience a necessity for end users and a strategic relationship builder for MSPs, as well as why and how MSPs can boost net revenue retention with their clients. Then they’re joined by Avihay Nathan of Palo Alto Networks for an insider’s take on both the challenges and opportunities of agentic AI security. And finally, one last thing: Ever wished there was a way on long drives to heed the call of nature without pulling off the road? Problem solved! Discussed in this episode:Business Resilience and the System of SpeedNew Survey Highlights Gap Between Perceived AI Readiness and Tested Disaster Recovery CapabilityAutonomous but Not Controlled: AI Agent Incidents Now Common in EnterprisesAgentic AI’s Scary Security RisksChinese car company patents voice-activated 'in-vehicle toilet' Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored. 

Erick and Rich discuss what Anthropic’s Mythos Preview model and Project Glasswing initiative portend for the future of security in managed services as well as how to turn your service desk into a powerful extension of your sales organization. Then, live from the Channel Partners Conference & Expo in Las Vegas, they’re joined by Robert DeMarzo of conference host Informa for an insider’s take on in-person events in the age of AI as well as Peter Kujawa of ConnectWise for a conversation about the latest MSP benchmark data. And finally, one last thing: Why a pro soccer club in Dusseldorf replaced Coach Beginning with Coach End. Discussed in this episode:ByRichard Stiennon: Mythos Preview Is a Break-Glass MomentFrom beginning to end: Soccer team switches two coaches with opposite names Some guests on this podcast are clients of Channel Mastered.Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

In this special bonus episode of MSP Chat, sponsored by Datto, Erick and Rich talk about why there’s still plenty of growth potential in backup and security for MSPs and why their clients need help in both areas now more than ever, as well as why speed is the ultimate competitive advantage for MSPs and how to cultivate it. Then they’re joined by Kaseya’s Adam Marget for a look at why cyber resilience solutions should be part of every MSP's service offerings and why every end user needs cyber resilience. And finally, one last thing: When those cute items you see on a store shelf turn out to be lifelike because they’re alive.  Discussed in this episode:2026 Kaseya Cybersecurity Outlook ReportBackup and recovery solutionsRethinking cyber resilience for modern ITOwl found napping on antique store shelf in New YorkReal-life possum found hiding in soft-toy display at Tasmanian airport

Erick and Rich discuss why anyone using or selling LLM tokens badly needs FinOps help, as well as why an MSP’s onboarding process determines how long new clients stay, how much they spend, and how profitable they become. Then they’re joined by Rev.io’s Evan Rice for a conversation about why MSPs are the logical candidate to own the agentic layer at SMBs, and how they can go about doing it. And finally, one last thing: We’ve had it with these &*$%-ing bees on this &*$%-ing plane. Discussed in this episode:Balancing AI innovation and cost: The new FinOps mandateRev.io Doesn’t Fear Claude Code. It Loves It.North Carolina flight delayed by bee swarm on turbine Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Treeline, a new kind of venture capital-backed MSP with interesting implications for the competitive landscape, as well as tips for driving more business with clients by clarifying your value proposition. Then they’re joined by Michael Crean of SonicWall for a look at the interesting and sobering results of the company’s 2026 Cyber Protect Report. And finally, one last thing: The most European robbery ever, and its amusing aftermath. Discussed in this episode:Treeline Raises $25 Million to Reinvent IT ServicesSonicWall Reframes Annual Research Around SMB Protection Outcomes, Reveals the Seven Deadly Sins in 2026 Cyber Protect ReportThieves steal 12 tons of KitKat bars in Europe chocolate heistHow a Massive KitKat Heist Turned Into Crisis PR Gold Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Live from the 2026 RSA Conference in San Francisco, Erick and Rich discuss the puzzling lack of interest in AI governance among MSPs and a go-giver lead generation concept proven to work by Erick himself. Then they’re joined by Jeff Loehr and Joe Rojas of MSP consultancy Start Grow Manage for a fun and fact-filled conversation about lead generation, sales meeting success, employee motivation, and operational efficiency. And finally, one last thing: You know spring has finally arrived when they’re burning socks in Annapolis. Discussed in this episode:Closing the AI Governance GapStart Grow Manage home pageDecades ago, a Maryland sailor burned his winter socks. Now it's a spring tradition Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss MSP-as-a-Service, a new outsourcing option for newcomers to managed services and existing MSPs who need more time to go all-in on building an AI practice, plus three practical steps any MSP can take to ensure they’re dedicating time to growth, margin protection, and leadership instead of fighting fires all day. Then they’re joined by ex-MSP and current thought leader Alex Stanton for an insightful conversation about what MSP rollups, cyber resilience, and AI herald for the future of managed services. And finally, one last thing: the crazy price paid at auction for a Flamin’ Hot Cheeto shaped like a Pokemon character. Discussed in this episode:Summit Holdings Launches “MSP-as-a-Service” Operating Model to Help MSPs Scale Faster and Increase Recurring RevenueFurther thoughts on AI and managed services from Alex Stanton:Mapping the Next Golden Age of Managed ServicesAI “Systems of Action” Have Worrying Implications for PSA Vendors'Cheetozard' auction results in a Guinness World Record Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored. 

Erick and Rich talk about why Slide’s Series B funding round, the MSP Well initiative, and GTIA’s 2026 Community and Councils Forum all underscore why community is more important than ever in the channel. Then Erick explains why reviewing client profitability on anything other than a company-by-company basis is guesswork, and Rich speaks with GTIA research czar Carolyn April about the 2026 State of the Channel Report. And finally, one last thing: the chicken-wing flavored, protein-packed espresso martini you never knew you wanted. Discussed in this episode:Slide Raises $70 Million Series B Led by General Catalyst to Expand Its Business Continuity and Disaster Recovery (BCDR) Platform for Managed Service ProvidersMSP Well websiteBuffalo Wild Wings unveils wing-flavored protein espresso martini Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss recent evidence about security awareness and alert fatigue that show why outsourced, AI-based automation must play a critical part in how MSPs protect their clients, as well as practical ways to enforce proper security with your clients rather than rely on the good intentions of their employees. Then they’re joined by Robin Ody of Omdia for an in-depth conversation about the analyst firm’s 2026 MSP Trends and Predictions Report. And finally, TWO last things: an illustration of the wrong way to incorporate voice AI in the call center and a follow-up on Erick’s suggestion last week that MSPs use AI to practice for big client meetings.  Discussed in this episode:Cybercrime Victimization Climbs to Record High 44% Over Five-Year PeriodNew N‑able and Futurum Report Reveals How AI is Reshaping Cyber ResilienceOverview of Omdia 2026 MSP Trends and Predictions ReportCallers to Washington state hotline press 2 for Spanish and get accented AI English insteadSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the right and wrong way to think about automating customer relationships with AI, as well as the connection between scalable service delivery and attractive exit prices. Then they’re joined by ScalePad CEO Chris Day for a deep dive into some of the surprising findings in that company’s recent MSP Trends report. And finally, one last thing: prepping for your performance review with an AI-powered version of the boss. Discussed in this episode:MSPs Need to Accelerate AI Evolution. Distributors Say They Can Help.ScalePad MSP Trends Report 2026Uber employees have an AI clone of CEO Dara Khosrowshahi — and use 'Dara AI' before talking to the big boss himself Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the reasons MSPs need to be implementing AI automation tools and the risk limits they should consider when doing so, as well as concrete strategies for growing profits and exit value by simplifying your tool stack and customer base. Then they’re joined by Pinar Ormeci of Lexful to discuss that company’s ambitious new AI-native system of record for MSPs. And finally, one last thing: A boxing ring TKO in which the “T” stands for toupee rather than technical. Discussed in this episode:Summary of Omdia’s 2026 MSP predictionsLexful Goes God-Mode on AIBoxer loses hairpiece in the ring and blames mother’s shampoo Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss why the channel’s AI maturity is stuck in a three-year rut according to IDC and what MSPs can do about it, plus strategies for converting focus and discipline into accelerated growth. Then they’re joined by the managing director of partner programs for Google Cloud, Phil Larson, for an insider’s take on opportunities for MSPs in cloud and AI. And finally, one last thing: how a real-life Jimmy Neutron produced nuclear fusion in his home lab. Discussed in this episode:AI is a Growing Business Yet Risky Bet for Channel PartnersIDC North America Partner Landscape 2025: Vendor Relations, Cloud Marketplaces, and DistributionIntroducing Google Cloud Partner Network: What partners should knowDallas 12-year-old achieves nuclear fusion after four years of effort Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Lexful’s ambitions to build the ultimate AI-native data repository for MSPs, as well as proven strategies for updating your managed services prices between renewals. Then they’re joined by M&A expert Abraham Garver of FOCUS Investment Banking for an insider’s take on today’s exit environment for MSPs and the rise of “mega mega” MSPs with nine-figure top lines. And finally, one last thing: A Seattle Seahawks fan who’s even more excited about this weekend’s Super Bowl than Rich because a home team victory will result in his first haircut in over a decade. Discussed in this episode:AI-Native IT Documentation Platform Redefines How MSPs Work, Solving Pain Points and Generating Value in Real TimeMega MSPs Are Old News. Say Hello to the Mega Megas.By Abraham Garver: Unlocking Higher MSP Multiples: How Peer Group M&A Outshines Conference ConnectionsSeahawks fan hasn’t cut his hair since Super Bowl 49 loss, won’t until Seattle wins again Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the impact that security and AI maturity are having on MSP valuations and three concrete techniques for increasing valuations by increasing EBITDA. Then they’re joined by Michael Assraf, CEO and founder of Flamingo, to explore that company’s unconventional open-source approach to MSP tooling. And finally, one last thing: A data-based look at the most overused buzzwords in email, and a confession by Erick and Rich that they use most of them. Discussed in this episode:Flamingo home page (including links to OpenMSP and OpenFrame)Flamingo’s Unorthodox Plan to Turn MSP Systems of Record into Loss LeadersThe Top 10 Most Overused Email Buzzwords Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss what ConnectWise buying zofiQ says about the future of AI automation and tool stacks for MSPs and how to make sales excellence as important a part of your culture as technical excellence. Then they’re joined by two top executives from Thread for an inside look at AI-powered service desk automation from a leading vendor in the field. And finally, one last thing: an incident involving a Waymo in Phoenix that might inspire you to delay your first ride in a self-driving car. Discussed in this episode:ConnectWise To Acquire zofiQ—Bringing AI-Powered Automation to IT Solution ProvidersMSP Chat interview with Lee Silverstone of zofiQA Channelholic article on ThreadWaymo passenger flees after car drives on Phoenix light rail tracks Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the easily overlooked opportunity for MSPs in AI prep work like implementing infrastructure and how MSPs can prepare themselves operationally to meet rising end user demand for AI services and solutions. Then they’re joined by Dave Sobel of The Business of Tech podcast to discuss his recent acquisition of an MSP community and education resource, and what it says about the current and future needs of smaller MSPs at a time when larger ones are commanding more attention. And finally, one last thing: How deepfake monkeys conquered St. Louis. Discussed in this episode:Ingram Micro’s Crawl, Walk, Run Strategy for Partner AIOmdia: Data centre, AI services and cloud marketplaces to drive partner growth in 2026Gartner Forecasts Worldwide IT Spending to Grow 9.8% in 2026, Exceeding $6 Trillion For the First TimeThe Business of Tech podcastMSP Radio Acquires Small Biz Thoughts and IT Service Provider UniversityA Welcome Investment in the Spirit of MSP CommunityMonkeys are on the loose in St. Louis and AI is complicating efforts to capture them Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss why the rise of AI-native “systems of action” poses a potential threat to the future of PSA solutions, as well as strategies for building an effective, valuation-boosting MSP leadership team. Then they’re joined by Kevin Lancaster, CEO of BetterTracker and Channel Program, for a must-hear conversation about what AI means for the long-term competitiveness of smaller MSPs. And finally, one last thing: a phishing attack involving actual fish, or aquatic creatures anyway. Discussed in this episode:AI “Systems of Action” Have Worrying Implications for PSA VendorsBy Kevin Lancaster: MSPs, the AI $hit is about to get realBy Kevin Lancaster: The 2026 AI Maturity Model for MSPsMicrosoft Discovers MSPs. Again.The Case of the $400,000 Massachusetts Lobster Heist Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss overcoming the gap between employer enthusiasm toward AI and employee mistrust, plus strategies MSPs can use for transitioning from IT provider to business consultant. Then they’re joined by Jason Ulacio of informer to explore the thinking behind Microsoft’s Intune for MSP program and the opportunity that initiative presents MSPs. And finally, one last thing: guess what the Merriam-Webster dictionary’s world of the year for 2025 was. Discussed in this episode:AI’s potential excites executives and investors, but general public remains skeptical, survey saysCEOs to Keep Spending on AI, Despite Spotty ReturnsFathom Insights: Rising AI Use, Rising Calls for ActionHow People Around the World View AIMicrosoft Discovers MSPs. Again.Microsoft Intune Blog: Addressing multi-tenant management challenges for MSPs with Microsoft Intune and partner innovationsMerriam-Webster names ‘slop’ the word of the year Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss what MSPs should make of AI-native, venture-funded MSP rollup Shield Technology Partners working side-by-side with OpenAI and hiring a C-level Palantir executive as its new CEO, as well as how and why to design your MSP for exit readiness even if you’re not selling today. Then they’re joined by ConnectWise CEO Manny Rivelo to explore AI’s long-term implications for MSPs and ConnectWise itself. And finally, one last thing: Just in time for holiday gift giving, there’s now drunk raccoon merch. Discussed in this episode:Jim Siders joins Shield Technology Partners as Chief Executive OfficerMerch commemorating drunk Virginia raccoon raises over $250,000 for animal shelterSNL’s drunk raccoon sketchTrashed panda merch Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored. 

Erick and Rich talk about strategies for changing endpoint and network management from increasingly commoditized services to profit engines, as well as three strategies for accelerating MSP growth in AI, cloud, and remote productivity. Then they’re joined by Cisco execs Tim Coogan and Elisabeth De Dobbeleer to discuss the new Cisco 360 partner program and the channel analysis behind it. And finally, one last thing: A jail break story about a failed attempt to break IN to a South Carolina prison with a stash of steak, weed, crab legs, cigarettes, and Old Bay. Discussed in this episode:News Flash: Networks and Endpoints Still ExistCisco 360 Partner Program Empowers Partners to Drive Profitability in an AI EraCisco Simplifies Security for Managed Service Providers, Accelerating Their Hybrid Mesh Firewall Deployments and Business GrowthDrone drops crab legs, steak and weed into South Carolina prison: “Folks were planning an early holiday Old Bay crab boil” Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Veeam’s addition of AI data to its data protection mission and what that says more broadly about challenges and opportunities in security for MSPs, as well as concrete tactics for retaining good clients and filtering out bad ones in 2026. Then they’re joined by Corey Nachreiner of WatchGuard for a conversation about AI in security generally and agentic AI in security specifically, as well as an early look at predictions in security for the new year. And finally, one last thing: a raccoon that got drunk as a skunk in a liquor store. Discussed in this episode:Veeam Data Platform v13 Launches and Redefines the Standard for Cyber Resilience, Advanced Data Protection, Security and Identity Controls, and AI-Powered IntelligenceA New Era for Accelerating Safe AI at Scale: Veeam to Acquire Securiti AI; Unifies Data Resilience with DSPM, Privacy and AI TrustRaccoon goes on drunken rampage in Virginia liquor store and passes out on bathroom floor Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Just in time for Thanksgiving, Erick and Rich celebrate 100 episodes of MSP Chat by trading thoughts on the show’s most thought-provoking, headline-grabbing, memory-making conversations. Then, just for fun, they share their favorite “One Last Thing” segments of the podcast in a conversation featuring return appearances by Charizard the Cheeto and Wally the emotional support alligator. Discussed in this episode:Episode 5: Navigating the Managed Services Landscape in the Cloud AgeEpisode 20: Cracking the Code on MSP RelationshipsEpisode 27: Why M&A is Still OK for MSPsEpisode 59: End Game of End GamesEpisode 62: Rough is EnoughEpisode 66: It Takes a Community to Secure an End UserEpisode 71: Don’t Buy VoldemortEpisode 74: No Timmies AllowedEpisode 76: Human to HumanEpisode 77: 75 Days of UptimeEpisode 88: From the Server Room to the BoardroomEpisode 95: Kirk Versus Picard Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Or is it caffeine fowl? You decide after listening to Erick and Rich discuss why venture capital funds are flooding into makers of AI software for SMBs and MSPs, plus tips on the most effective ways for MSPs to get lead generation mileage out of brief local speaking opportunities. Then they’re joined by Jennifer Anaya, SVP of global marketing at Ingram Micro, and Cheryl Rang, Ingram’s VP of technology solutions, for back-to-back interviews about the power of community, the opportunity for partners in AI and security, and much more. And finally, one last thing: a story about a parrot in South Korea who resembles humans not only in its ability to speak but in its love for coffee too. Discussed in this episode:Top Down Ventures Announces Release of its Industry-first Research Report: The State of MSP Capital in the Age of AICoffee-stealing parrot captured at South Korean cafeSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich talk about the refreshing candor with which ConnectWise acknowledged past mistakes at its IT Nation Connect event and whether or not MSPs will buy into its plans to do better going forward, as well as tips for getting attention and coverage from reporters like Rich. Then they’re joined by Slide co-founders Austin McChord and Michael Fass for an inside look at that company’s next-generation data protection solution for MSPs and, yes, its pending lawsuit with Kaseya. And finally, one last thing: A Düsseldorf museum tour that for just €7 extra comes with an authentically grumpy German guide. Discussed in this episode:MSP Chat Episode 35: Achieving Media MasteryFrom The Business of Tech: Datto Sues Slide: An Exclusive Investigative Report‘I try to make them feel as ignorant as possible’: German museum’s ‘grumpy guide’ is surprise hit Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Join Erick and Rich for a whirlwind visit to two tech conferences. First up is Ingram Micro’s ONE show, where they discuss the new definition of distribution in the age of AI as well as tactics for raising rates in response to rising costs without alienating your clients. Then, in a conversation recorded live at ConnectWise’s IT Nation 2025 conference, they bring you a conversation about the future of AI-powered service delivery with Lee Silverstone of service desk automation vendor zofiQ. And finally, one last thing: Forget about the World Series. The winner-take-all contest to watch is the Parallel Parking Championship. Discussed in this episode:zofiQ Takes on the Hyperautomation Big BoysYes, There’s a Parallel Parking Championship, and I Was a ContenderSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the MCP protocol’s underappreciated security risks and how to handle clients at financial risk due to the ongoing federal government shutdown. Then they’re joined by Glenn Mathis, CEO of Integris, to discuss a giant MSP’s strategy for using AI internally, selling it to clients, avoiding commoditization, and more. And finally, one last thing: why haunted car washes are the Halloween thrill ride America’s been waiting for. Discussed in this episode:Security Risks of Agentic AI: A Model Context Protocol (MCP) IntroductionSecuring the Agentic AI Control Plane: Announcing the MCP Security Resource CenterSome guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss whether or not we’re in an AI bubble and how much MSPs should be worried if we are, before exploring strategies for increasing profitability and client retention by selling outcomes instead of tools. Then they’re joined by the co-founders of Titan, a venture capital-backed A.I. software company/MSP rollup that’s building something totally new in the history of managed services. And finally, one last thing: Beware the surf-jacking otter of Santa Cruz, Calif. Discussed in this episode:Are we in an AI bubble?Move Over, Private Equity. Venture Capital is Investing in MSPs Too.Shield Technology Partners Is Building Something Totally New in Managed ServicesSurfboard-stealing otter attacks resume at California beach Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss the opportunity in cybersecurity for MSPs and the skills gap contributing to it, plus three strategies for coping with competition, client budget constraints, and profitability pressures. Then they moderate a panel discussion on operational excellence recorded live and onstage during the recent Kaseya DattoCon event in Miami. And finally, one last thing: why Cypress has as many cats as people. Discussed in this episode:Forrester Research: Global Cybersecurity Spending To Exceed $300B By 2029CompTIA: State of Cybersecurity 2025Cyprus has a cat problem: One feline for every resident Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss what Kaseya buying INKY says about the strategies stand-alone security vendors must embrace to remain competitive in the future, and why stand-alone MSPs competing with rollups should employ those strategies too. Then they’re joined by legendary MSP guru and Kaseya Chief Community Officer Gary Pica for an insightful exploration of the past, present, and future of managed services. And finally, one last thing: why the only bad time to in a Nobel Prize is in the middle of a digital detox. Discussed in this episode:Kaseya Acquires Leading AI-Powered Email Security Provider INKYNobel committee unable to reach prize winner who is ‘living his best life’ hiking off grid Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich talk about some flaws in that now famous MIT study suggesting that 95% of AI pilots end in failure, as well as three techniques for setting the right AI expectations with your clients. Then they're joined by TD SYNNEX executives Ed Morales and Tracy Holtz for wide-ranging conversations about AI and cloud computing recorded live at the recent TD SYNNEX Inspire conference. And finally, one last thing: who police in San Bruno, California gave the ticket to when a self-driving car made an illegal turn. Discussed in this episode:MIT report: 95% of generative AI pilots at companies are failingMusic by Ed MoralesCalifornia police pull over a self-driving Waymo for an illegal U-turn, but they can’t ticket Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Microsoft’s newfound interest in SMBs and their MSP partners as a source of cloud growth, plus three tips for avoiding client onboarding chaos. Then Rich is joined by Michael George and Dee Zepf of Syncro for a conversation about Microsoft’s large and expanding role in the world of SMB technology and what it means both for managed service providers and vendors like Syncro. And finally, one last thing: proof from a BBC nature documentary that dolphins like getting stoned as much as humans do. Discussed in this episode:Microsoft blog post: Addressing multi-tenant management challenges for MSPs with Microsoft Intune and partner innovationsDolphins ‘deliberately get high’ on puffer fish nerve toxins by carefully chewing and passing them around Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss Syncro CEO Michael George’s take on why Microsoft is destined to dominate the managed services landscape and what that means for MSPs and vendors alike, as well as techniques for protecting your clients from deepfake phishing attacks and other AI-powered cyberthreats. Then Rich is joined by Art Gross, CEO of Breach Secure Now, to discuss his new book, From Prompt to Profit: The MSP Playbook for AI-Driven Client Success. And finally, one last thing: A new AI-based podcast service that spells certain doom for Erick, Rich, and MSP Chat. Discussed in this episode:From Prompt to Profit: The MSP Playbook for AI-Driven Client Success5,000 Podcasts. 3,000 Episodes a Week. $1 Cost Per Episode — Behind an AI Start Up’s Plan Some guests on this podcast are clients of Channel Mastered. Compensation plays no part in their appearance or the content of the discussion unless the episode they appear on is a “bonus episode” explicitly labeled as sponsored.

Erick and Rich discuss DarcyIQ and Titan, two companies whose rapid progress in AI for managed services underscores why MSPs need to take AI seriously ASAP, plus three tips for scaling your business without adding headcount. Then they’re joined by Arlin Sorensen of ConnectWise to discuss why MSPs need to think now about the legacy they’ll eventually leave behind, and start planning for that someday today. And finally, one last thing: a few easy ways to become a Guinness World Records holder. Discussed in this episode:General Catalyst’s Latest AI Bet Is in ITNew AI Platform DarcyIQ Automates Deal Flow and Accelerates Win Rates for B2B Services CompaniesIT Nation Evolve peer groupsSignup form for Arlin’s private daily morning email list that covers faith, family, and businessFor information on Arlin’s success to significance peer groups and legacy planning, email [email protected] World Records turns 70 - and highlights some unclaimed records

Erick and Rich talk about the growing need for virtual Chief AI Officers and what it means for an MSP to be one, plus tips on selling cybersecurity services without actually selling. Then they’re joined by Joel Abramson and Mark Scott of Top Down Ventures for a venture capital investor’s take on today’s managed services market. And finally, one last thing: the gritty tale of a woman who spent three weeks digging in the dirt for an engagement ring diamond, and found one. Discussed in this episode:The Challenges to Ensuring Information Is Secure, Compliant and Ready for AI, a report by OpenText and Ponemon InstituteTop Down VenturesThe Top Down LinkedIn NewsletterTop Down Horizons eventA New York woman dug for 3 weeks to find her own engagement ring diamond

Erick and Rich discuss the present-day opportunity for MSPs in cloud FinOps and the emerging need for AI FinOps, plus some proven advice for managing service desk capacity for maximum efficiency and minimum employee churn. Then Rich is joined by Kaseya CEO Rania Succar for an in-depth look at her thoughts on AI solutions for SMBs, MCP interfaces, community, culture, and more. And finally, one last thing: the munchies doom loop of eating THC-laden pizza at a pizzeria. Discussed in this episode:Kaseya Wants to Sell AI Through MSPs As Well As To ThemPizzeria mishap left at least 85 people intoxicated with THC after infused oil used for dough

Erick and Rich discuss the multiple issues (and yes, AI is one of them) leading more MSPs to consider joining forces with a rollup rather than go it alone, plus three criteria MSPs should apply when evaluating vendor partner programs. Then they’re joined by Canalys analyst Jay McBain for an insight-packed look at the massive opportunity for MSPs in AI, and why getting in on it early is so important. And finally, one last thing: Why you should probably do a little research online before agreeing to meet with a diplomat from Westarctica. Discussed in this episode:The New Rules of Partner Programs are Still TBD10 Tips for Modern MSPs to Evaluate Vendor Channel ProgramsMan posed as an ambassador and ran a fake embassy, Indian police say

Erick and Rich discuss early examples of how MSPs are re-tooling their workforce for the age of agentic AI as well as effective, empathetic techniques for addressing underperforming staff members. Then they’re joined by Chris Black, technical advisor at Xurrent, for a look at that company’s “right of observability” product strategy, and what it says about evolving MSP tool requirements as they grow and mature. And finally, one last thing: An opportunity for friends of a Danish zoo to show their support by feeding their pets to a lynx. Discussed in this episode:Building the Workforce of the AI FutureHow a “People Company” is Going AIThere’s No ServiceNow for MSPs. Xurrent Aims to Close That Gap.A zoo in Denmark asked patrons to donate their pets. Not as attractions, but for food

Erick and Rich discuss why LLMs, chatbots, and MCP could combine to revolutionize the way technicians interact with RMM, PSA, and other line-of-business systems, as well as how delivering business resilience rather mere uptime can be a ticket to sticky, profitable client relationships. Then they’re joined by Ryan Morris, who serves MSP Chat parent company Channel Mastered as chief channel program strategist, for an insightful expert look at why and how partner programs are changing in response to a newly complex channel ecosystem. And finally, one last thing we can summarize in three simple words: Radioactive. Wasp. Nest.  Discussed in this episode:Is Your Next Help Desk Tech Named Claude?Slide is Living in the MCP FutureRadioactive wasp nest found at site where US once made nuclear bombs

Live and side by side at GTIA’s ChannelCon event in Nashville, Erick and Rich discuss Pax8’s bold plan to re-invent marketplaces for the agentic AI era, and a roadmap MSPs can use to get started in AI services before it’s too late. Then they’re joined by back-to-back interview guests—Will Brooks from UKON and Eric Altamura from SPECTRA—to explore two of several emerging models for turning cyber insurance from a stressful headache into value-adding risk management conversation. And finally, one last thing: Chuck E. Cheese has been busted for credit card fraud. Discussed in this episode:UKON Announces Strategic Partnerships with Cork, CreditPulse, Blackpoint Cyber, and SeedPodSpectra Releases Certification of Resilience for MSPs; Launches Advisory Board‘Come with me, Chuck E’: Florida police arrest mascot for credit card fraud as children look on

Erick and Rich discuss the pros and cons for MSPs of placing bets on today’s emerging crop of startup AI automation vendors and the best practice roadmap for helping clients make AI-driven business model shifts. Then they’re joined by Juan Fernandez, founder of MSP Owners Group, to discuss that recently launched company’s unique, private equity-free approach to building a PE-style MSP platform. And finally, one last thing: the seething mass of giant, hairy spiders that customs inspectors in Germany recently found in a container supposedly full of chocolate cake. Discussed in this episode:AI-Native Approaches to AI-Era Managed ServicesInfiltrateIQ’s AI to Z Approach to Pen TestingThere are Riches in Niches in AI for MSPsMSP Owners GroupRoughly 1,500 tarantulas found stuffed in boxes meant for chocolate cake

Wondering about the future of managed services? Erick and Rich (who’s back after a multi-week absence) explain why new research from Barracuda suggests offering consultative security and AI services to midsize businesses is a big part of the answer. Then they share three specific tips for cross-selling and upselling services like that to your existing client base, before getting a big-picture perspective on AI, security, and more from Mike DePalma, vice president of business development at OpenText. And finally, one last thing: laboratory proof that when it isn’t furiously hallucinating, AI can successfully complete gallbladder surgery all by itself. Discussed in this episode:73% of Organizations With up to 2,000 Employees Rely on MSPs to Manage the Security Challenges of GrowthAI-Enabled Robot Performs Gallbladder Surgery

This week, Erick flies solo and dives into the newly released 2025 MSP 501 rankings from Channel Futures—the industry’s gold standard for identifying top-performing managed service providers. He breaks down why this data-driven list matters, how it boosts credibility, attracts vendors, and fuels internal momentum, and highlights the top trends driving this year’s winners—like AI adoption, security-first service models, and compliance-driven growth. Next, he explains why the time is now to update your LinkedIn profile. Then, Erick shares insights from his on-site interview with Bill Brandel, EVP and President, North America at Ingram Micro, recorded live at the Trust X Alliance Unplugged 2025 event in Philadelphia, where “connection” was the theme of the day. And finally, one last thing: Sewer Gators are real—and they’re living their best lives underground in Florida. Discussed in this episode:Why the MSP 501 matters (even if you didn’t make the list)Ingram Micro TrustX Alliance Unplugged 2025One Last Thing: Florida’s not-so-mythical alligator in the sewer system

A staggering 16 billion credentials linked to major services—Apple, Facebook, Google, and more—have just been confirmed leaked and Erick explores the grim reality and potential aftermath, and what it means for MSPs, as well as the types of AI services MSPs can deliver to their customers to increase their strategic value to them as well as their recurring revenue. Then, Erick is joined by Pax8’s Chief Product Officer, Libby McIlhaney, at Pax8 Beyond 25, for a look at AI’s impact and opportunity for Pax8 and its partners. Discussed in this episode:16 Billion Apple, Facebook, Google And Other Passwords LeakedPax8 Beyond 2025 Day 1 RecapStanley Cup damaged as the Florida Panthers celebrate a second straight championship

Fresh from the floor at Pax8 Beyond 25, Erick and Rich break down one of the event’s biggest announcements: the launch of PAX8’s new Integrations Hub and what it reveals about the evolving role of distribution, marketplaces, and the push for vendor interoperability in the cloud-first era; and how MSPs are using AI to write RFPs, win funding, and transform their client relationships.Then Erick is joined by Nerdio CRO Joseph Landes on the floor at Pax8 Beyond 25 for a wide-ranging discussion on best practices for building a profitable Microsoft Cloud practice, what’s next for Nerdio partners, and why automation is key to solving the MSP talent gap.Discussed in this episode:Pax8’s Integrations Hub: Marketplace Stickiness via AutomationNerdio’s AI-Powered Cloud Management Platform

Speaking just after this week’s ConnectWise IT Nation Secure event, Erick and Rich discuss the simplified new ConnectWise Pro subscription plan and best practices for optimizing your client agreements before an exit. Then they’re joined by John Pagliuca, president and CEO of N-able, and Mike Adler, N-able’s chief technology and product officer, for a discussion about why N-able believes MSPs should invest in XDR and MDR solutions rather than SIEM systems of the kind recently introduced by ConnectWise and Kaseya. And finally, one last thing: A woman in Australia who did 7,079 pull-ups in 24 hours.  Discussed in this episode:ConnectWise Launches PSA Powered by Asio and ConnectWise Pro at IT Nation Secure 2025Australian woman completes 7,079 pull-ups in 24 hours

Erick and Rich ponder the tradeoffs of using an all-inclusive managed services platform versus going with best of breed as well as techniques for migrating managed service clients to a standardized services stack. Then they’re joined by Yoav Susz, general manager for the U.S. at Atera, to discuss Atera Autopilot, a fully autonomous AI-powered help desk tool now in general availability. And finally, one last thing: a look at Internet Roadtrip, the world’s slowest massive multiplayer online game. Discussed in this episode:In Defense of SeamsAtera Autopilot is (Almost Eerily) LiveThousands of people have embarked on a virtual road trip via Google Street View

Erick and Rich discuss why vendors are introducing partner loyalty programs and how MSPs can cement their position as trusted advisors while locking in revenue by aligning IT budget discussions with a client’s financial planning cycles. Then they’re joined by Jessica McDowell, TD SYNNEX’s senior vice president of North American marketing and digital customer success, for a conversation about AI, community, marketplaces, and the changing relationship between partners and distributors. And finally, one last thing: a look at LegoGPT, the AI killer app we’ve all been waiting for. Discussed in this episode:TD SYNNEX Brings B2C Rewards to B2B RelationshipsTD SYNNEX Partner Loyalty programTD SYNNEX PartnerLINK programLegoGPT is here to make your blocky dreams come true